A novel synthesis of enantiopure octahydropyrrolo[3,4-b]pyrroles by intramolecular [3+2] dipolar cycloaddition on chiral perhydro-1,3-benzoxazines

被引：32

作者：

Pedrosa, R ^{[1
]}

Andrés, C ^{[1
]}

de las Heras, L ^{[1
]}

Nieto, J ^{[1
]}

机构：

[1] Univ Valladolid, Fac Ciencias, Dept Quim Organ, E-47011 Valladolid, Spain

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 15期

关键词：

D O I：

10.1021/ol0261377

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] Condensation of N-substituted glycines with chiral 3-allyl-2-formyl perhydro-1,3-benzoxazines forms an azomethine ylide that cyclizes to give octahydropyrrolo[3,4-b]pyrrole derivatives. The [3 + 2] dipolar cycloadditions are stereoespecific leading to a single diastereoisomer. The chemical yields are dependent on the reaction temperature and the presence or absence of a base.

引用

页码：2513 / 2516

页数：4

共 55 条

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